Location: East Shore Acres, Boca Grande
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5020 GROUPER HOLE CT, BOCA GRANDE, FL 33921
$4,675,000115 Days on yellowkey MLS ID: D6145898
Bed: 3 Bath: 3.5 Gar: 4 Liv Area Sq Ft: 2951 Built: 2002 Tax: $71,279 (2025)Community: East Shore AcresSpa: NoSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$71,279
Elementary School: The Island School
High School: Lemon Bay High
Tax Year: 2025
Middle School: L.A. Ainger Middle
Remarks: Located on Gasparilla Island beyond a private driveway, this one-of-a-kind retreat spans generous acreage and captures panoramic bay and coastal water views. Positioned on 1.88 acres and framed by native landscaping, the serene setting feels worlds away, yet remains just minutes from the charm of Boca Grande village. Spanning 2,951 square feet of refined living space with a total footprint of 6,287 square feet, the residence features three bedrooms plus a study or bonus room that can easily serve as a fourth bedroom, along with three-and-a-half baths. An interior elevator services all floors, ensuring effortless access throughout. The interiors reflect a sophisticated coastal aesthetic, highlighted by light-colored hardwood floors and thoughtfully designed living spaces. The study features a wet bar, opens to an exterior porch, and offers a perfect spot for stargazing, while the upstairs primary suite enjoys its own private porch—both providing sweeping Bay views and front-row seats to abundant wildlife, including osprey, pelicans, and egrets. An expansive porch running the length of the home invites morning coffee with sunrises over the water and evenings bathed in soft sunset hues. Electric hurricane shutters provide peace of mind, while the three-car, climate-controlled garage plus dedicated golf cart space adds everyday convenience. Leisurely bike rides or golf cart trips along the paved path lead directly into the village of Boca Grande, known for exceptional dining, unique shopping, world-class fishing, and outstanding boating. Properties of this size, setting, and water-view presence are exceptionally rare on the island, making this a truly special opportunity.
Listing is courtesy of: MICHAEL SAUNDERS & CO. - BOCA (941-964-2000)
Listing Agent: Kathleen Turner (941-234-7643)
9 PEEKINS COVE DR, BOCA GRANDE, FL 33921
$4,150,000116 Days on yellowkey MLS ID: D6145854
0 Days Off yellowkey (back on 5/26/2026)
Bed: 3 Bath: 3.0 Gar: 6 Liv Area Sq Ft: 2299 Built: 2006 Tax: $51,372 (2025)Community: East Shore AcresSingle Family
Taxes:$51,372
Remarks: Under contract-accepting backup offers. A truly exceptional waterfront estate offering approximately 2,300 square feet of refined coastal living, this residence enjoys over 100 feet of coveted frontage on Gasparilla Sound with a private dock, covered boat lift, and deep-water access in the serene setting of Peekins Cove. Built in 2006 by Bowen Construction, the home showcases thoughtful craftsmanship with impact windows and doors, elevator-ready design, and two beautifully appointed living levels. The main level is designed for effortless entertaining, featuring two guest suites with private en-suite baths, an open-concept kitchen overlooking the living and dining areas, a laundry room, and tile flooring throughout. The living and dining spaces are filled with natural light and accented by tray ceilings, recessed lighting, and elegant crown molding. A spacious covered deck extends from the living area, providing the perfect vantage point to take in stunning sunrises over the harbor and tranquil water views. The kitchen offers solid wood cabinetry, Corian countertops, stainless steel appliances, an ice maker, and ample storage, ideal for both everyday living and hosting guests. Upstairs, the primary suite serves as a private sanctuary, complete with a generous bath featuring dual vanities with granite countertops, abundant storage, a jetted soaking tub, and a walk-in closet. A private deck off the primary suite captures sweeping views of Peekins Cove and Gasparilla Sound, while the adjacent loft offers flexible space for a sitting area, office, or reading retreat. An oversized 1,560-square-foot climate-controlled garage provides exceptional space for multiple vehicles, golf carts, and water toys. The property also offers room to add a pool, enhancing its resort-style potential. Offered fully turnkey, this exceptional waterfront home delivers a rare combination of privacy, craftsmanship, and premier boating access on Gasparilla Sound.
Listing is courtesy of: GULF TO BAY SOTHEBY'S INTERNAT (941-964-0115)
Listing Agent: Cynthia Crawford (941-662-1495)
4070 LOOMIS AVE, BOCA GRANDE, FL 33921
$12,500,000194 Days on yellowkey MLS ID: D6144651
Bed: 4 Bath: 4.5 Gar: 5 Liv Area Sq Ft: 5472 Built: 1997 Tax: $72,087 (2025)Community: East Shore Acres IiSpa: YesSingle Family
Taxes:$72,087
Remarks: Nestled on a rare 1.6-acre waterfront parcel with views of Gasparilla Sound is a coastal masterpiece that has just undergone a complete, top-to-bottom remodel by PCI, embracing a serene coastal theme with light, airy colors throughout. Conveniently located on Loomis Avenue, just moments from the charming shops, restaurants, and amenities of historic downtown Boca Grande, this exquisite estate offers tranquility with sweeping breathtaking unobstructed water views. Boasting an impressive 159 feet of prime waterfront, the property features 4 spacious bedrooms, a versatile flex den room, 4.5 luxurious baths, and multiple inviting living areas designed for seamless flow and relaxation. The chef’s dream kitchen is outfitted with premium Wolf brand appliances, perfect for culinary enthusiasts. Convenience abounds with laundry facilities on both the lower and top floors. Step outside to one of the largest pools on Boca Grande, ideal for lavish gatherings, complemented by a grand main-floor patio area and a private master suite balcony on the top floor—both perfect for entertaining guests in style. The estate includes a massive 5-6 car garage with convenient side-entry doors, ample parking via an elegant circle drive, hurricane-rated windows and doors for peace of mind, and a private elevator for effortless access between levels. An open floor plan enhances the home’s light-filled ambiance, while mature, lush landscaping envelops the grounds in tropical serenity. This is more than a home—it’s a slice of paradise, where luxury meets the laid-back charm of island living, all just a short stroll or bike ride from town.
Listing Agent: Jeff Moore (941-855-0737)
14 GROUPER HOLE DR, BOCA GRANDE, FL 33921
$10,825,000162 Days on yellowkey MLS ID: N6141937
Bed: 5 Bath: 5.5 Gar: 4 Liv Area Sq Ft: 6207 Built: 1997 Tax: $56,560 (2025)Community: East Shore AcresSingle Family
Taxes:$56,560
Elementary School: None
High School: None
Middle School: None
Remarks: 2 DEEP-WATER DOCKS AND A COVERED 7,000 LB LIFT. 5 BEDROOMS AND 5.5 BATHROOMS. MYRTHA POOL. INDOOR GUN RANGE. NO FIXED BRIDGES TO GULF WATERS. ROOF 2017. Welcome to a true Sportsman’s Paradise at 14 Grouper Hole Drive on Gasparilla Island in Boca Grande, Florida. This exceptional waterfront estate offers an unparalleled lifestyle, where breathtaking views of the Gasparilla Sound greet you the moment you step through the grand double doors. Designed for both adventure and relaxation, this residence seamlessly blends refined elegance with world-class amenities. The main living area is on the second floor, accessible by a three-stop elevator. A bright foyer leads into the expansive living room, which is open to the third floor, creating an impressive sense of space with soaring ceilings. The dining area flows effortlessly into the kitchen, where a beautiful bay window breakfast nook offers the perfect setting to enjoy morning coffee with stunning water views. The kitchen features a WOLF gas stove, a Sub-Zero paneled refrigerator, a spacious pantry, and a breakfast bar. French doors from the living room open onto a large screened deck—ideal for entertaining or unwinding as boats pass by. The second floor hosts three guest bedrooms, each with nearly floor-to-ceiling windows and en-suite bathrooms. A half bath and a well-appointed laundry room are also on this level. A striking catwalk on the third floor, adorned with a sculptural iron railing, overlooks the living space below while offering sweeping views of the Sound. The luxurious primary suite is a serene retreat, with private access to an open-air deck to enjoy the waterfront breeze. The en-suite bath features dual vanities, a walk-in shower, and a separate soaking tub. A generous walk-in closet with custom shelving provides ample storage. An additional sitting area with a bay window offers yet another breathtaking vantage point. A well-appointed fifth bedroom, also with mesmerizing water views and an en-suite bath, is located opposite the primary suite. The estate’s crown jewel is the extraordinary sports pavilion, seamlessly connected to the main home. Designed for ultimate recreation, it features an indoor/outdoor sitting and dining area with a retractable mosquito screen and fire pit. Inside, a stylish living space and fully equipped kitchen boast Viking appliances, Kendall Cambria Quartz countertops, a built-in bar refrigerator, and an ice machine. At its heart is the Myrtha Ozone Pool—one of Florida’s most advanced residential pools. Competition-length, with stainless steel bolted technology for durability, it features a European lighting system, the only one of its kind in North America. Exceptionally pure, the water is free of chlorine and salt, making it pristine enough to drink. The pool is both heated and cooled for year-round enjoyment, with a standalone hot tub nearby. Remote controlled hurricane shutters add to piece of mind. The sports pavilion also includes a private, air-conditioned Pilates studio and areas for ping pong and pool. For shooting enthusiasts, the state-of-the-art gun range features two dedicated lanes—one for archery and one for firearms. Equipped with a high-tech camera system for precision accuracy, a retractable target retrievals, advanced bullet entrapment, and sound suppression, this range ensures top tier performance.
Listing is courtesy of: KELLER WILLIAMS ISLAND LIFE REAL ESTATE (941-254-6467)
Listing Agent: Michelle Hupp (941-773-5464)
5010 GROUPER HOLE CT, BOCA GRANDE, FL 33921
$4,500,000144 Days on yellowkey MLS ID: D6145351
Bed: 4 Bath: 2.5 Liv Area Sq Ft: 2648 Built: 1986 Tax: $5,933 (2024)Community: East Shore AcresSingle Family
Taxes:$5,933
Tax Year: 2024
Remarks: Tucked away on a quiet cul-de-sac and set well back on a private shelled driveway, this elevated two-story residence offers a rare blend of acreage, privacy, and timeless Florida craftsmanship. The home’s welcoming entry is framed by two stately columns, creating an elegant sense of arrival. Situated on 1.7 acres private estate the property enjoys tranquil water views through the mangroves with partial views of Gasparilla Sound, offering a serene Old Florida setting. The location also provides close proximity to the Boca Grande Club, combining privacy with convenient access to island amenities. Built in 1986 by respected builder Dick Yusk, this four-bedroom, two-and-a-half-bath single-family home features a thoughtfully designed floor plan, including two primary bedrooms, ideal for multigenerational living or hosting guests. The great room is a standout, showcasing vaulted ceilings, tongue-and-groove oak hardwood flooring, beadboard detailing, and chair rail accents that create warmth and architectural character. Bedrooms are comfortably carpeted, while the bathrooms are finished with tile. The open kitchen is dramatic and light-filled, highlighted by a vaulted ceiling with atrium windows, tile flooring, and a breakfast bar that opens to the dining area—perfect for everyday living and entertaining. A versatile den provides additional flexibility and may be used as a home office, library, or sitting room. The outdoor setting embraces the property’s natural surroundings with mature landscaping, an irrigation system, and a peaceful, private atmosphere that complements the creekside location. An outdoor shower adds coastal practicality, while the expansive grounds offer ample opportunity to enjoy the outdoors or further customize the property to suit your lifestyle. The home is constructed with a HardiPlank Cement Siding, topped with a metal roof, and equipped with 175mph rated PGT hurricane windows for durability and peace of mind. Additional features include zoned 2.5-ton central air conditioning, an indoor laundry room, French door entry, and an inviting front porch. Completing the property is an oversized 24’ x 28’ detached two-car garage with workshop, ideal for storage, hobbies, or recreational equipment. The home is serviced by a private pre-treatment effluent pump. Public water and sewer is onsite. Furnishings are negotiable, offering a potential turnkey opportunity. This is a rare offering for those seeking privacy, acreage, and waterfront tranquility—where classic Florida architecture, natural beauty, and thoughtful design come together in a peaceful and sought-after setting.
Listing Agent: Richard Hugger (941-270-2816)
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